The Joy of Dumb Questions: Knocking on the Door to Knowledge

A Culture of Asking Dumb Questions

The same was true at Interleaf. I had left academia thinking I was taking a step down in terms of intellectual stimulation. Perhaps knowledge managers who come from another academic discipline feel similarly. In any case, my snobbery was misplaced. Not only were Interleafers as smart as professional philosophers, and not only were they creating something materially good for the world, their culture allowed something that I’d rarely seen in academia: dumb questions. 

For example, I remember early on asking one of the font designers exactly what a font was. Remember, this was before we all become font jockeys thanks to the sophistication of our document software. Were they bitmaps or vectors, and, by the way, what did those two terms mean? How does the software scale fonts up or down arbitrarily? Can some of the bits be a different color so the font could have soft edges or hard outlines?

I spent 8 years at Interleaf asking dumb questions and not once being made to feel dumb. In part, I think this was because the engineers accurately sensed that I was genuinely interested in what they were doing. But more important, we were all working on a single project that depended on everyone understanding it. But there were so many parts to it—graphics formats and manipulation, document management processes, networking protocols, GUI design, vertical market needs, financing, printer rasterization hardware, four different hardware platforms, and on and on. Acknowledging being dumb in pertinent areas was the only viable path toward the company’s shared goals. 

Such an environment can’t afford there being any shame in not knowing. I’ve found that to be true of all the great development teams I’ve worked with. It was a part of Interleaf’s entire culture, from the CEO to marketing schlubs like me.

I stepped back into academics 20 years later as a researcher at Harvard’s Berkman Klein Center, which has explicitly cultivated a culture that encourages conversations across disciplinary lines and strongly discourages “gotcha” moments. It helps that the researchers cover a wide range of topics, so it’s natural to see every encounter as an opportunity to learn, including by asking dumb questions.

So why is philosophy so prone to bad conversations? To begin with, I don’t have any quantifiable data that it actually is, just a bunch of experience. Much less do I have a rigorous theory to explain the phenomenon, if it is indeed a phenomenon.

The best I can come up with is that across different schools of philosophy, there is often little agreement about the grounds of knowledge. Without that, there is often no good way to settle an argument in terms of its truth. But engineers have an excellent way: Does the idea work? In philosophy, often the only way you can tell that you’ve won is by reducing your opponent to a stammering hulk.

Fortunately, there’s a way to fight back. If you’re a knowledge manager, work on creating a culture that discourages knowledge one-upmanship. Make sure that your knowledgebase has answers at every level of experience and knowledge. And, as a leader, embrace chances to ask dumb questions without fear or hesitation. After all, dumbness acknowledged is the most powerful knowledge tool we have.